


Peep Show

by Ariyana



Series: Kinktober 2020 [6]
Category: The Umbrella Academy (TV)
Genre: Creepy The Handler (Umbrella Academy), Cussing, Dom/sub Undertones, Dominance, Don't copy to another site, Dubious Consent, Exhibitionism, F/M, First Time, First Time Blow Jobs, Forced Consent, Foreplay, Hand Jobs, Humiliation, Kinktober 2020, Loss of Virginity, Older Number Five, Oral Sex, Penis In Vagina Sex, Pet Names, Power Imbalance, Power Play, Praise Kink, Sexual Content, Sexual Tension, Stranger Sex, Suggestive Themes, Touch Desensitizing, Touch-Starved, Vaginal Sex, Voyeurism
Language: English
Status: Completed
Published: 2020-10-16
Updated: 2020-10-16
Packaged: 2021-03-08 19:29:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,509
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27042025
Author URL: https://archiveofourown.org/users/Ariyana/pseuds/Ariyana
Summary: The Handler thinks it is about time that Five learn a thing or two about touch, whether he wants to learn or not. However she's more for instructing rather than getting her hands dirty.Kinktober 2020: Featuring Pairing, Five/Handler, Five/A Nameless StrangerDay Fourteen: Stranger Sex/Exhibitionism/Voyeurism
Relationships: Number Five | The Boy/Original Character(s), Number Five | The Boy/The Handler (Umbrella Academy)
Series: Kinktober 2020 [6]
Series URL: https://archiveofourown.org/series/1950295
Comments: 4
Kudos: 34





	Peep Show

**Author's Note:**

> Yep, still behind on the kinktober challenge but here's the one for Day 14.
> 
> Day 14: Stranger Sex | Frottage | Facial | Exhibitionism/Voyeurism
> 
> I combined Stranger Sex with Exhibitionism/Voyeurism. This is yet another pairing I didn't think I would write about, but the actual sex doesn't happen between them. There are implications that this sort of arrangement happened between them more often than not, which would be the reason why he was able to rock Lila's world in ["I Hate You!"](https://archiveofourown.org/works/27016690). So it is related to that verse in a way.

He and the Handler never really fucked, but that hadn’t meant she wasn’t involved in his sex life. It was one of those games she liked to play with him, but he had learned fairly early on it was better to indulge her than refuse her. The first time it happened, he had technically been a virgin. His only experience being the times that he had fantasized with Dolores. Sometimes his mind would almost fool him into thinking she was the real thing, but nothing could have prepared him for the actual real thing.

He didn’t even know the woman’s name, she had shown up with the Handler at his hotel room, ready to do whatever the Handler told her to do. He had enough self-awareness to know the girl was lovely. A petite dark haired woman with green eyes like his own and perfectly pale skin.

“Do you like her, Five?” The Handler had asked as she petted the woman’s hair in front of him. Idly she pushed a strand of the woman’s pitch black hair behind her ear as she leaned in to press a kiss to the shell of the woman’s ear.

“Does it matter?” Five asked, shifting in discomfort as he watched the sight. His body reacting despite his brain wanting to be anywhere but there.

“Of course, I wouldn’t want you to fuck someone you thought looked tragic.” She replied matter of factly.

Five’s eyes widened, caught completely off guard by her words. “W-what?!” He sputtered, taking a step back.

“I want you to fuck her, Five. You really need the release. All those years stuck in a wasteland without _true_ touch. It’s too heartbreaking to think about.” She said in that coy yet forced sad tone of hers, that already had him feeling like he wanted to strangle her. Clearly she was mocking him. He hated it. He hated her, but she was his boss. There wasn’t much he could do, refusing her wasn’t a wise decision. Especially if he wanted to get through his contract and see his family again.

He had felt like a deer caught in the headlights as the woman closed the gap between them, pressing her voluptuous body into him. Her blouse was tight hugging her curves, while showing off the swell of her cleavage. His eyes couldn’t help but be drawn to her bosom, watching the rise and fall of her chest as she stood flush against him.

“Five you are far too overdressed. Won’t you help relieve him of some of that clothing dear?” The Handler asked, the woman.

She said nothing as she locked gazes with Five. Her expression was weirdly blank as she reached for his tie and began loosening it with quick nimble fingers. Before he could really process what was happening, she had pulled his tie free and had started on unbuttoning his shirt. His breathing hitched as he felt her fingers against the skin of his neck. Touch was such a foreign concept after forty-two years in the wasteland. Soon she had pushed the white fabric of his dress shirt off of his shoulders and began pulling on his undershirt, ready to pull it up and over his head, but he stopped her. His hands held firm to her wrists.

She blinked, giving him a questioning gaze but otherwise said nothing.

“What’s wrong, Five?” The Handler asked from her new location, perched on the only chair in the room as if she were watching a movie. All she needed was a bowl of popcorn to complete the look. 

Five found himself, biting down on his lip, trying to keep the scathing comment from coming out. “Are you seriously going to sit there and watch this like some sort of theatrical performance?” He asked incredulously.

“Well I went through all the trouble to find you a suitable partner. It’s not much to ask to see that my efforts don’t go to waste.” She replied without missing a beat.

The blood practically drained from his face as he looked at her in complete disgust. His natural instinct was to protest, but he quickly bit his lip, thinking better of his retort. Slowly he released the woman’s wrists, allowing her to remove his shirt, leaving his chest bare. Never had he felt so exposed as he did in that moment. All the scars and years of abuse that he heaped on his body in the name of survival were suddenly on display for both this mystery woman and the Handler. He was a fifty-five year old man, who had been seriously malnourished during his time in the Apocalypse. Even with the rigorous training and surgeries the Commission put him through, he held no delusions of grandeur over his appearance. While he wasn’t necessarily ashamed of his body, that didn’t mean he wanted it on display for just anyone to see.

However the woman merely leaned into him, nuzzling her face against the crook of his neck, while her hands smoothed over his chest, her fingers idly tracing his various scars. Her hot breath on his neck, followed by the wet feel of her tongue lapping against his pulse was more soothing than he could have imagined.

“You’re such a good boy, Five.” The Handler cooed, bringing his attention back to her. His half-lidded gaze locked with the Handler’s and she gave him such a devious little smile.

Suddenly the sound of his zipper filled the silence and then he felt the woman’s hand slip into his pants to slowly pull his cock from its fabric prison. He was already half hard as she began to stroke him. His breath shuddered at the sensation. No one had ever touched his cock but him. It was strange to feel the ministrations of a hand other than his own. Yet he couldn’t deny that she knew what she was doing. She seemed to innately know just how much pressure to apply to his shaft as she made soothing jerking motions. The beating sound of his skin filling the air along with the small moans escaping his lips.

Lightly the Handler chuckled. “Now that is a look of bliss, I see.” She said, lighting up a cigarette as she leaned back in the chair, evidently enjoying the show.

He opened his mouth to retort, but was immediately distracted when the woman dropped to her knees in front of him and began nuzzling his cock against her cheek. Reverently she placed a kiss at the head of his cock, before licking the precum off the tip and then she was swallowing him whole. He could only watch in awe and wonder as he had no concept of a blowjob. His father had given them the lecture about sex, puberty and masturbation, but he had only covered the basics about intercourse, keeping it completely clinical with no mention of things like foreplay or oral sex. 

He choked back a groan as she took him further into her mouth, stroking him with that wet warmth that had his cock tingling as it grew harder and that much closer to release. His hands landed in her hair, holding on to it for dear life as she worked him over with her mouth and hands. He could feel a deep burning in his belly as that familiar tightened coil threatened to sprung loose.

“That’s enough, dear. He won’t last much longer if you keep that up.” The Handler commanded with a tsk as the woman pulled back as ordered. Five involuntarily whimpered at the lost of contact.

The woman pulled his pants and boxers down to his feet, before pushing him onto the bed. Within moments she had stripped down to nothing and maneuvered herself to straddle his hips. Her hot folds brushing against his cock, caused him to let a low moan. Instinctively he placed his hands on her hips as she gently grabbed his shaft and guided him against her entrance. His breath quickened as she slowly impaled herself on his throbbing cock. His eyes practically rolled into the back of his head as he was bombarded with all these new sensations. She was so hot, so wet, so fucking _tight_ , like a vice around his cock. He groaned in spite of himself, his fingers digging into the flesh of her hips as he held onto her for dear life. 

Nothing could have prepared him for the way she rolled her hips against his, riding his cock as if he were some prized horse. The Handler’s smoke filled the room, along with her coy laugh as she watched him lose his virginity to a complete stranger. However that wasn’t the only time she watched him fuck and be fucked. While it wasn’t the least bit professional for her to do this sort of thing to him, she didn’t seem to care and he was still in no position to complain. Thus he took all the lessons to heart as he would learn to weaponize them and use to his own advantage.


End file.
